EP0033255A1 - Oxim-Derivate von Erythromycin A, ihre Herstellung, ihre Verwendung als Pharmazeutika und sie enthaltende pharmazeutische Zusammensetzungen - Google Patents

Oxim-Derivate von Erythromycin A, ihre Herstellung, ihre Verwendung als Pharmazeutika und sie enthaltende pharmazeutische Zusammensetzungen Download PDF

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Publication number
EP0033255A1
EP0033255A1 EP81400026A EP81400026A EP0033255A1 EP 0033255 A1 EP0033255 A1 EP 0033255A1 EP 81400026 A EP81400026 A EP 81400026A EP 81400026 A EP81400026 A EP 81400026A EP 0033255 A1 EP0033255 A1 EP 0033255A1
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EP
European Patent Office
Prior art keywords
radical
formula
product
erythromycin
products
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP81400026A
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English (en)
French (fr)
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EP0033255B1 (de
Inventor
Solange Gouin D'ambrieres
André Lutz
Jean-Claude Gasc
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Sanofi Aventis France
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Roussel Uclaf SA
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Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Priority to AT81400026T priority Critical patent/ATE9161T1/de
Publication of EP0033255A1 publication Critical patent/EP0033255A1/de
Application granted granted Critical
Publication of EP0033255B1 publication Critical patent/EP0033255B1/de
Priority to KE356685A priority patent/KE3566A/xx
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

Definitions

  • the present invention relates to novel oximes derived from erythromycin A, their preparation, their use as medicaments and the pharmaceutical compositions containing them.
  • radicals examples include radicals obtained by the action of amines, sulfides, phenates, alcoholates, or a halohydric acid such as hydrofluoric acid.
  • the values of B can be chosen from the values indicated above for R when R represents an optionally substituted alkyloxy, aryloxy or aralkyloxy radical.
  • the optionally substituted alkyl, aryl, aralkyl values may be the corresponding values such as methyl, ethyl, propyl, phenyl, benzyl, and the like.
  • radicals of the acetal type there may be mentioned more particularly the radicals of the acetal type.
  • the following radicals are preferred: 1,3-dioxolan-2-yl, dimethoxymethyl, diethoxymethyl.
  • Esterified carboxyl radicals which can be represented by R are alkoxycarbonyl radicals having at most 7 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, propyloxycarbonyl, isopropyloxycarbonyl and butyloxycarbonyl.
  • salts formed with the carboxyl group mention may be made of the sodium, potassium, lithium, calcium, magnesium or ammonium salts or the salts formed with the organic amine bases such as trimethylamine, diethylamine, triethylamine or tris (hydroxymethyl) aminomethane.
  • acyl radicals mention may in particular be made of acetyl, propionyl, butyryl, isobutyl, n-valeryl, isovaleryl, tert-valeryl and pivalyl radicals.
  • Ra values mention may be made in particular of alkanoyl radicals such as acetyl, propionyl, n-butyl, isobutyryl, n-valeryl, isovaleryl, pivalyl and acryloyl.
  • alkanoyl radicals such as acetyl, propionyl, n-butyl, isobutyryl, n-valeryl, isovaleryl, pivalyl and acryloyl.
  • salts of the present derivatives with mineral or organic acids mention may be made of the salts formed with acetic acids. , Propionic acid, tri- fluoroacetic, maleic, tartaric, formulationthanesulfoni q ue, benzenesulfonic, p-toluenesulfonic, hydrochloric, hydrobromic, hydroiodic, sulfuric, phosphoric and especially stearic, ethylsuccinic or laurylsulfu- America.
  • the product of formula (III) is used in the form of a salt.
  • the hydrohalide preferably hydrochloride or hydrobromide.
  • the reaction is then preferably carried out in a buffered medium, for example in the presence of an excess of an organic amino base such as triethylamine or an organic acid-alkaline salt mixture of this acid such as a mixture acetic acid sodium acetate.
  • an organic amino base such as triethylamine or an organic acid-alkaline salt mixture of this acid such as a mixture acetic acid sodium acetate.
  • an alcoholic solvent such as methanol or ethanol and preferably in an anhydrous medium.
  • reaction of the product of formula (V) with the product of formula (IV) is preferably carried out in the presence of a base such as triethylamine or in the presence of sodium or potassium carbonate or sodium or potassium carbonate. calcium or barium.
  • a polar solvent such as acetone, dimethylformamide; dimethylsulfoxide or hexamethylphosphotriamide.
  • a polar solvent such as acetone, dimethylformamide; dimethylsulfoxide or hexamethylphosphotriamide.
  • an ether such as ethyl ether, tetrahydrofuran or dioxane.
  • the reactions can be conducted at temperatures between room temperature and the reflux temperature of the solvent.
  • the reaction can be prolonged several hours or even days to obtain a complete transformation.
  • Salification and esterification are carried out according to the usual methods.
  • the invention more particularly relates to a process for the preparation of the products of formula (I), characterized in that a product of formula (II) is treated with a hydrochloride or a hydrobromide of a product of formula (III) and in that one operates in the presence of an organic amine base or an alkaline earth metal carbonate, and a process characterized in that a product of formula (IV) is treated with a product of formula (V) in the presence a base selected from the group consisting of carbonate and sodium or potassium hydrogen carbonate, calcium carbonate, barium carbonate and sodium hydride.
  • the products of general formula (I) have a very good antibiotic activity on gram-like bacteria such as staphylococci, streptococci, pneumococci.
  • boils anthrax, phlegmons, eesipeles, primitive or post-influenza acute staphylococci, bronchopneumonia, pulmonary suppuration, streptococcal diseases such as acute tonsillitis, ear infections, sinusitis, scarlet fever, pneumococcal diseases such as pneumonia, bronchitis; brucellosis, diphtheria, gonorrhea.
  • the products of the present invention are also active against infections due to germs such as Haemophilus influenzae, Haemophilus Pertussis, Rickettsiae, Mycoplasma pneumoniae.
  • the subject of the present invention is therefore also, as medicaments and, in particular, antibiotic medicaments, the products of formula (I) as defined above, as well as their addition salts with pharmaceutically acceptable inorganic or organic acids. acceptable.
  • the invention more particularly relates, as medicaments and, especially, antibiotic drugs, the preferred products of formula (I) defined above and their pharmaceutically acceptable salts.
  • the invention extends to pharmaceutical compositions containing as active principle at least one of the drugs defined above.
  • compositions may be administered orally, rectally, parenterally, or locally by topical application to the skin and mucous membranes.
  • the preferred route is the oral route.
  • the active ingredient (s) can be incorporated into excipients usually employed in these pharmaceutical compositions, such as talc, gum arabic, lactose, starch, magnesium stearate, cocoa butter, aqueous or non aqueous vehicles. fatty substances of animal or vegetable origin, paraffinic derivatives, glycols, various wetting, dispersing or emulsifying agents, preservatives.
  • compositions may also be in the form of a powder intended to be dissolved extemporaneously in a suitable vehicle, for example sterile pyrogen-free water.
  • the dose administered varies according to the condition being treated, the subject, the route of administration and the product under consideration. It may be, for example, between 0.250 g and 4 g per day orally, in humans, with the product described in Example 1 or 5.
  • the products of formula (III) may for example be prepared according to the general method described in Angew. chem. 68, 1956 No. 8 p.303.
  • EXAMPLE 1 9- [O- (2-methoxyethoxy) methyl] oxime / erythromycin.
  • EXAMPLE 2 9- [O- / 2- (4-chloro-ohenoxy) ethyl] oxime / erythromycin.
  • EXAMPLE 5 9- [O- / 2- (dimethylamino) ethyl] oxime / erythromycin.
  • the mixture is then cooled, the insoluble material is filtered and rinsed with acetone.
  • the amorphous product obtained is filtered, rinsed with water and dried in an oven. This preparation is repeated three times. A total of 335.6 g of crude product is obtained, a quantitative yield.
  • the crystals are filtered and then washed with acetone at 40% ice water.
  • the crystals are filtered. Rinsed and washed with 100 cm3 of acetone at 40% water. It is dried at 40 ° C. under vacuum.
  • This product is redissolved in about 100 cm3 of acetone and stirred at about 50 ° C with activated charcoal for 10 minutes. Filtered hot.
  • Example 9 In the procedure described in Example 9, the hexamethylphosphotriamide-ether mixture is replaced by dimethylformamide. 0.75 g of erythromycin oxime is placed in 3.5 cm3 of dimethylformamide. 53 mg of sodium hydride are added in half. Stir 15 minutes and add 0.158 g of dimethylaminoethyl chloride hydrochloride and 53 g of sodium hydride at half. After 4 hours at room temperature. 29 mg of dimethylaminoethyl chloride hydrochloride and 11 mg of sodium hydride are added in half. It is stirred overnight, saturated with carbon dioxide, poured into 35 cm3 of water, drained, rinsed, taken up in chloroform, dried and evaporated. The residue is crystallized in 2 cm3 of pentane. 0.428 g of expected product is obtained. After taking up the mother liquors, a second jet of 210 mg product identical to the products obtained in Examples 5, 8 and 9 is obtained.
  • a series of tubes are prepared in which the same amount of sterile nutrient medium is distributed. Increasing amounts of the test product are dispensed into each tube, and then each tube is inoculated with a bacterial strain.
  • C.M.I minimum inhibitory concentrations
  • mice We studied the action of some products exam- p les and erythromycin on experimental Staphylococcus aureus infection in mice.
  • mice weighing 21 g were infested by intraperitoneal injection of 0.5 cm 3 of a 22-hour broth culture at pH 7 of Staphylococcus aureus strain 5446, diluted 1/6 with physiological water.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
EP81400026A 1980-01-11 1981-01-09 Oxim-Derivate von Erythromycin A, ihre Herstellung, ihre Verwendung als Pharmazeutika und sie enthaltende pharmazeutische Zusammensetzungen Expired EP0033255B1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AT81400026T ATE9161T1 (de) 1980-01-11 1981-01-09 Oxim-derivate von erythromycin a, ihre herstellung, ihre verwendung als pharmazeutika und sie enthaltende pharmazeutische zusammensetzungen.
KE356685A KE3566A (en) 1980-01-11 1985-10-01 Nouvelles oximes derivatives de l'erythromycine a,leur preparation,leur application comme medicaments et les compositions pharmaceutiques les renfermant

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8000566 1980-01-11
FR8000566A FR2473525A1 (fr) 1980-01-11 1980-01-11 Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments

Publications (2)

Publication Number Publication Date
EP0033255A1 true EP0033255A1 (de) 1981-08-05
EP0033255B1 EP0033255B1 (de) 1984-08-29

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EP81400026A Expired EP0033255B1 (de) 1980-01-11 1981-01-09 Oxim-Derivate von Erythromycin A, ihre Herstellung, ihre Verwendung als Pharmazeutika und sie enthaltende pharmazeutische Zusammensetzungen

Country Status (25)

Country Link
US (1) US4349545A (de)
EP (1) EP0033255B1 (de)
JP (1) JPS56100799A (de)
KR (1) KR850000964B1 (de)
AU (1) AU537247B2 (de)
BG (1) BG61369B2 (de)
CA (1) CA1162535A (de)
CY (1) CY1319A (de)
DE (1) DE3165720D1 (de)
DK (1) DK157878C (de)
ES (1) ES8200702A1 (de)
FI (1) FI69473C (de)
FR (1) FR2473525A1 (de)
GR (1) GR73103B (de)
GT (1) GT198500080A (de)
HK (1) HK586A (de)
HU (1) HU187760B (de)
IE (1) IE50680B1 (de)
IL (1) IL61808A (de)
LU (1) LU88283I2 (de)
MY (1) MY8500984A (de)
NL (1) NL930097I2 (de)
OA (1) OA06719A (de)
PT (1) PT72331B (de)
ZA (1) ZA808108B (de)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2534588A2 (fr) * 1982-10-15 1984-04-20 Roussel Uclaf Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments
EP0158467A3 (en) * 1984-04-06 1986-03-19 Taisho Pharmaceutical Co. Ltd Method for selective methylation of erythromycin a derivatives
EP0422843A3 (en) * 1989-10-07 1991-09-18 Taisho Pharmaceutical Co. Ltd 6-0 methylerythromycin a oxime derivatives
WO1996018633A1 (en) * 1994-12-13 1996-06-20 Zambon Group S.P.A. Erythromycin a 9-0-oxime derivatives endowed with antibiotic activity
RU2222333C1 (ru) * 2003-03-06 2004-01-27 Открытое акционерное общество "Химико-фармацевтический комбинат "Акрихин" Фармацевтическая композиция с антибактериальной активностью и способ ее получения
WO2014077712A1 (en) 2012-11-14 2014-05-22 Gdański Unwersytet Medyczny Solid lipid nanoparticles of roxithromycin for hair loss or acne
WO2017174593A1 (fr) 2016-04-07 2017-10-12 Universite Claude Bernard Lyon 1 Nouvelles compositions antivirales pour le traitement de la grippe

Families Citing this family (36)

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US4526889A (en) * 1982-11-15 1985-07-02 Pfizer Inc. Epimeric azahomoerythromycin A derivative, intermediates and method of use
DK149776C (da) * 1984-01-06 1987-04-21 Orion Yhtymae Oy Antibiotisk virksom erytromycinforbindelse og praeparat indeholdende forbindelsen
JPS61103890A (ja) * 1984-10-26 1986-05-22 Taisho Pharmaceut Co Ltd ６−０−メチルエリスロマイシンａ誘導体
EP0201166B1 (de) 1985-03-12 1990-02-07 Beecham Group Plc Erythromycin-Derivate
JPS61229895A (ja) * 1985-04-03 1986-10-14 Nippon Zeon Co Ltd 保護化デス−ｎ−メチルエリスロマイシン誘導体
US4740502A (en) * 1986-06-20 1988-04-26 Abbott Laboratories Semisynthetic erythromycin antibiotics
DE3782994T2 (de) 1986-09-18 1993-04-08 Taisho Pharma Co Ltd Erythromycin-a-derivate und verfahren zu ihrer herstellung.
JP2751385B2 (ja) * 1988-05-19 1998-05-18 大正製薬株式会社 エリスロマイシンａオキシム及びその塩の製造方法
US5075289A (en) * 1988-06-07 1991-12-24 Abbott Laboratories 9-r-azacyclic erythromycin antibiotics
US5912331A (en) * 1991-03-15 1999-06-15 Merck & Co., Inc. Process for the preparation of 9-deoxo-9(Z)-hydroxyiminoerythromycin A
CA2062932A1 (en) 1991-03-15 1992-09-16 Robert R. Wilkening 9-deoxo-9(z)-hydroxyiminoerythromycin a and o-derivatives thereof
US5985844A (en) * 1992-03-26 1999-11-16 Merck & Co., Inc. Homoerythromycin A derivatives modified at the 4"-and 8A-positions
US5189159A (en) * 1992-04-02 1993-02-23 Merck & Co., Inc. 8a-AZA-8a-homoerythromycin cyclic iminoethers
ES2036472B1 (es) * 1991-10-01 1994-03-01 Prodesfarma Sa Procedimiento de obtencion de eritromicina 9-(0-((2-metoxietoxi)metil)oxima) (roxitromicina).
US5210235A (en) * 1992-08-26 1993-05-11 Merck & Co., Inc. Methods of elaborating erythromycin fragments into amine-containing fragments of azalide antibiotics
US5332807A (en) * 1993-04-14 1994-07-26 Merck & Co., Inc. Process of producing 8A- and 9A-azalide antibiotics
KR970702725A (ko) * 1994-04-26 1997-06-10 노부히로 나리따 비소세포 폐암 치료용 의약 조성물(Medicinal Composition as a Remedy for Nonsmall Cell Lung Cancer)
US5872229A (en) 1995-11-21 1999-02-16 Abbott Laboratories Process for 6-O-alkylation of erythromycin derivatives
FR2760017B1 (fr) * 1997-02-27 1999-04-30 Hoechst Marion Roussel Inc Nouveaux derives de l'erytromycine, leur procede de preparation et leur application comme medicaments
US5929219A (en) 1997-09-10 1999-07-27 Abbott Laboratories 9-hydrazone and 9-azine erythromycin derivatives and a process of making the same
PT102202B (pt) * 1998-09-10 2001-04-30 Hovione Sociedade Quimica S A Processo para a purificacao de roxitromicina
IN190782B (de) * 1998-09-30 2003-08-23 Max India Ltd
EP1004591B1 (de) * 1998-11-24 2003-04-09 Max India Limited Verfahren zur Herstellung von Roxithromycin und Derivate davon
AU783055B2 (en) * 1999-12-16 2005-09-22 Teva Pharmaceutical Industries Ltd. Processes for preparing clarithromycin polymorphs and novel polymorph IV
RU2002118308A (ru) 2000-01-11 2004-02-20 Тева Фамэситикл Индастрис Лтд. (Il) Способы получения полиморфных модификаций кларитромицина
HUP0302466A2 (hu) * 2000-02-29 2003-11-28 Teva Pharmaceutical Industries Ltd. Eljárások clarithromycin, clarithromycin intermedier, gyakorlatilag oximmentes clarithromycin és ezt tartalmazó gyógyszerkészítmény előállítására
HRP20020885B1 (en) 2002-11-11 2007-05-31 GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. SUBSTITUTED 9a-N-{N'-[4-(SULFONYL)PHENYLCARBAMOYL]}DERIVATIVES 9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHROMYCIN A AND 5-O-DESOZAMINYL-9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHRONOLIDE A
HRP20020991A2 (en) 2002-12-12 2005-02-28 Pliva-Istra�iva�ki institut d.o.o. N"-Substituted 9a-N-(N'-carbamoyl-Gamma-aminopropyl), 9a-N-(N'? -thiocarbamoyl-Gamma-aminopropyl), 9a-N-(N'-((Beta-cyanoethyl)-N'-carbamoyl-Gamma? -aminopropyl) and 9a-N-(N'-(Beta-cyanoethyl)-N'-thiocarbamoyl-Gamma? -aminopropyl) derivatives of 9-de
EP1435359A1 (de) * 2002-12-31 2004-07-07 Alembic Limited Verfahren zur Reinigung von Roxithromycin
WO2008023248A2 (en) 2006-08-24 2008-02-28 Wockhardt Research Centre Novel macrolides and ketolides having antimicrobial activity
US20090005326A1 (en) * 2007-06-26 2009-01-01 Idexx Laboratories, Inc. Single dose roxithromycin
WO2012076989A1 (en) 2010-12-09 2012-06-14 Wockhardt Limited Ketolide compounds
KR101567658B1 (ko) 2011-03-01 2015-11-09 욱크하르트 리미티드 케톨리드 중간체의 제조 방법
CN103619863B (zh) 2011-03-22 2016-03-16 沃克哈特有限公司 酮内酯化合物的制备方法
CN102219816A (zh) * 2011-05-12 2011-10-19 浙江国邦药业有限公司 一种罗红霉素的纯化方法
CN104163840A (zh) * 2013-08-30 2014-11-26 郑州后羿制药有限公司 一种罗红霉素的精制方法

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2534588A2 (fr) * 1982-10-15 1984-04-20 Roussel Uclaf Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments
EP0158467A3 (en) * 1984-04-06 1986-03-19 Taisho Pharmaceutical Co. Ltd Method for selective methylation of erythromycin a derivatives
EP0422843A3 (en) * 1989-10-07 1991-09-18 Taisho Pharmaceutical Co. Ltd 6-0 methylerythromycin a oxime derivatives
WO1996018633A1 (en) * 1994-12-13 1996-06-20 Zambon Group S.P.A. Erythromycin a 9-0-oxime derivatives endowed with antibiotic activity
LT4276B (lt) 1994-12-13 1998-01-26 Zambon Group S.P.A. Eritromicino a 9-o-oksimo dariniai, pasižymintys antibiotiniu aktyvumu
AP739A (en) * 1994-12-13 1999-03-24 Zambon Spa Erythromycin A 9-0-oxime derivatives endowed with antibiotic activity.
CN1046535C (zh) * 1994-12-13 1999-11-17 萨宝集团公司 红霉素a9－0－肟衍生物和含它们的药物组合物
MD1788G2 (ro) * 1994-12-13 2002-05-31 Zambon Group S.P.A. Derivaţi de 9-O-oximă ai Eritromicinei A, compoziţie farmaceutică pe baza lor şi metodă de tratament al bolilor infecţioase
RU2222333C1 (ru) * 2003-03-06 2004-01-27 Открытое акционерное общество "Химико-фармацевтический комбинат "Акрихин" Фармацевтическая композиция с антибактериальной активностью и способ ее получения
WO2014077712A1 (en) 2012-11-14 2014-05-22 Gdański Unwersytet Medyczny Solid lipid nanoparticles of roxithromycin for hair loss or acne
WO2017174593A1 (fr) 2016-04-07 2017-10-12 Universite Claude Bernard Lyon 1 Nouvelles compositions antivirales pour le traitement de la grippe

Also Published As

Publication number Publication date
PT72331B (fr) 1982-07-23
PT72331A (fr) 1981-02-01
GR73103B (de) 1984-02-02
IE810046L (en) 1981-07-11
ES498395A0 (es) 1981-11-01
NL930097I1 (nl) 1993-10-01
AU537247B2 (en) 1984-06-14
DE3165720D1 (en) 1984-10-04
DK157878C (da) 1990-07-30
NL930097I2 (nl) 1995-04-03
IE50680B1 (en) 1986-06-11
EP0033255B1 (de) 1984-08-29
DK157878B (da) 1990-02-26
FI69473B (fi) 1985-10-31
LU88283I2 (fr) 1994-09-09
ES8200702A1 (es) 1981-11-01
US4349545A (en) 1982-09-14
FR2473525B1 (de) 1983-04-15
CY1319A (en) 1986-03-28
KR830005258A (ko) 1983-08-03
JPS6237639B2 (de) 1987-08-13
IL61808A0 (en) 1981-01-30
ZA808108B (en) 1982-01-27
FI69473C (fi) 1986-02-10
CA1162535A (fr) 1984-02-21
GT198500080A (es) 1987-03-06
FR2473525A1 (fr) 1981-07-17
FI810042L (fi) 1981-07-12
HK586A (en) 1986-01-10
IL61808A (en) 1986-12-31
MY8500984A (en) 1985-12-31
AU6613181A (en) 1981-07-16
BG61369B2 (bg) 1997-06-30
OA06719A (fr) 1982-06-30
KR850000964B1 (ko) 1985-07-02
DK7881A (da) 1981-07-12
JPS56100799A (en) 1981-08-12
HU187760B (en) 1986-02-28

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